ChemSpider 2D Image | Butorphanol | C21H29NO2

Butorphanol

  • Molecular FormulaC21H29NO2
  • Average mass327.461 Da
  • Monoisotopic mass327.219818 Da
  • ChemSpider ID16735714
  • defined stereocentres - 3 of 3 defined stereocentres


More details:



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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(-)-BC 2627
(-)-Butorphanol
(-)-N-Cyclobutylmethyl-3,14-dihydroxymorphinan
17-(Cyclobutylmethyl)morphinan-3,14-diol [ACD/IUPAC Name]
17-(Cyclobutylmethyl)morphinan-3,14-diol [German] [ACD/IUPAC Name]
17-(Cyclobutylméthyl)morphinane-3,14-diol [French] [ACD/IUPAC Name]
255-808-8 [EINECS]
42408-82-2 [RN]
Butorfanol [Spanish] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

3620 [DBID]
8134188 [DBID]
C06863 [DBID]
D03197 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      N02AF01 Wikidata Q1185089
    • Chemical Class:

      Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the <element>N</element>-methyl group is substituted by cyclopropyl. A se mi-synthetic opioid agonist-antagonist analgesic, it is used as its (<element>S</element>,<element>S</element>)-tartaric acid salt for relief or moderate to severe pain. ChEBI CHEBI:3242
      Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A se; mi-synthetic opio id agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3242
      Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain. ChEBI CHEBI:3242

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 507.3±50.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.4 mmHg at 25°C
Enthalpy of Vaporization: 81.9±3.0 kJ/mol
Flash Point: 265.9±28.8 °C
Index of Refraction: 1.643
Molar Refractivity: 95.0±0.4 cm3
#H bond acceptors: 3
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 3.77
ACD/LogD (pH 5.5): 1.05
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 6.55
ACD/LogD (pH 7.4): 2.75
ACD/BCF (pH 7.4): 47.13
ACD/KOC (pH 7.4): 330.39
Polar Surface Area: 44 Å2
Polarizability: 37.6±0.5 10-24cm3
Surface Tension: 60.3±5.0 dyne/cm
Molar Volume: 262.7±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.37

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  437.82  (Adapted Stein & Brown method)
    Melting Pt (deg C):  183.55  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.12E-010  (Modified Grain method)
    Subcooled liquid VP: 1.41E-008 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  60.19
       log Kow used: 4.37 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  72.631 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Phenols

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.39E-014  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.240E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.37  (KowWin est)
  Log Kaw used:  -12.245  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  16.615
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1885
   Biowin2 (Non-Linear Model)     :   0.0029
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7758  (months      )
   Biowin4 (Primary Survey Model) :   2.7501  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1891
   Biowin6 (MITI Non-Linear Model):   0.0390
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.6258
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.88E-006 Pa (1.41E-008 mm Hg)
  Log Koa (Koawin est  ): 16.615
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.6 
       Octanol/air (Koa) model:  1.01E+004 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.983 
       Mackay model           :  0.992 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 274.7947 E-12 cm3/molecule-sec
      Half-Life =     0.039 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    28.025 Min
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.988 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  8.157E+004
      Log Koc:  4.912 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.663 (BCF = 460.1)
       log Kow used: 4.37 (estimated)

 Volatilization from Water:
    Henry LC:  1.39E-014 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 7.634E+010  hours   (3.181E+009 days)
    Half-Life from Model Lake : 8.328E+011  hours   (3.47E+010 days)

 Removal In Wastewater Treatment:
    Total removal:              49.06  percent
    Total biodegradation:        0.47  percent
    Total sludge adsorption:    48.59  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       4.93e-006       0.934        1000       
   Water     7.94            1.44e+003    1000       
   Soil      86.3            2.88e+003    1000       
   Sediment  5.78            1.3e+004     0          
     Persistence Time: 3.04e+003 hr




                    

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